Diastereoselective synthesis of alpha-tocopherol: a new concept for the formation of chromanols.
A diastereoselective synthesis of alpha-tocopherol 1 (93% de) was achieved via two key steps, (i) a highly diastereoselective Shi epoxidation of a trisubstituted alkene and (ii) an acid supported, "anti-Baldwin" epoxide ring opening under inversion of configuration leading to the 6-membered chromanol ring.
Chapelat
Julien
J
Department of Chemistry, University of Basel, Basel, Switzerland.
Buss
Axel
A
Chougnet
Antoinette
A
Woggon
Wolf-D
WD
D002839:Chromans / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D024502:alpha-Tocopherol / Q000138:chemical synthesis* / Q000737:chemistry
D002839:Chromans; D004852:Epoxy Compounds; C029141:2,2,5,7,8-pentamethyl-1-hydroxychroman; D024502:alpha-Tocopherol